US4774234A - Insecticide mixtures containing fatty acids - Google Patents
Insecticide mixtures containing fatty acids Download PDFInfo
- Publication number
- US4774234A US4774234A US07/118,305 US11830587A US4774234A US 4774234 A US4774234 A US 4774234A US 11830587 A US11830587 A US 11830587A US 4774234 A US4774234 A US 4774234A
- Authority
- US
- United States
- Prior art keywords
- insecticide
- acid
- fatty acid
- composition
- sis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
Definitions
- This invention is concerned with insecticides and enhancing their insecticidal effect using partial replacement compounds which are more environmentally acceptable.
- the pesticides generally fall into five major categories viz: chlorinated hydrocarbons e.g. DDT, lindane, methoxychlor, etc.; organophosphates e.g. malathion, dibrom, diazinon (trademark), phosphamidon, etc.; carbamate compounds e.g. baygon (trademark), sevin (trademark), zectran (trademark), etc.; inorganic compounds e.g. arsenic, sulphur, borax, etc.; and botanical compounds e.g. pyrethrum, strychnine, nicotine, etc.
- the chemical insecticides have been frequently used against major forest pests, e.g. DDT against spruce budworm, and have in many cases, been quite successful.
- the chemical insecticides with the exception of the botanical ones, have several disadvantages. Most of them are highly toxic to fish, wildlife, and humans and must be used with caution. They are usually not natural biological constituents and tend to persist for long lengths of time after their initial application. This is best exemplified by the chlorinated hydrocarbons which because of their persistence have passed through the animal food chain and caused egg shell thinning and egg breakage in many species of birds.
- C18:X acids especially oleic and linoleic and their salts in solution in concentrations from 0.25 to 5.0% in combination with the organophosphates, especially diazinon in a concentration range of 50 ppm to 50,000 ppm, were effective for the control of insect pests.
- the invention thus provides an insecticidal composition having enhanced insecticidal activity comprising:
- an insecticide active against defoliating insects selected from the group consisting of organic esters of phosphoric or thiophosphoric acid and carbamates, and mixtures thereof, and
- the invention includes a method of protecting susceptible plants against sucking insects or defoliating insects applying concurrently to the plant surfaces or directly to the insects, both (a) an insecticide active against defoliating insects selected from organic esters of phosphoric or thiophosphoric acids and carbamates, and mixtures thereof, and (b) an unsaturated fatty acid having 18 carbon atoms or its salt; the fatty acid compound being at least about 50% by wt. of (a)+(b).
- an insecticide active against defoliating insects selected from organic esters of phosphoric or thiophosphoric acids and carbamates, and mixtures thereof
- an unsaturated fatty acid having 18 carbon atoms or its salt the fatty acid compound being at least about 50% by wt. of (a)+(b).
- Preferably (a) and (b) are applied together as a mixture.
- the invention also includes a method of synergistically enhancing the insecticidal activity of an insecticide selected from the group consisting of organic esters of phosphoric or thiophosphoric acid and carbamates and carbamates and mixtures thereof, the method comprises adding to the insecticide an effective amount of a unsaturated fatty acid having 18 carbon atoms. In any case, the amount of the unsaturated fatty acid is at least the same amount as the insecticide.
- the fatty acid (b) is preferably selected from oleic acid, linoleic acid, their soaps (salts) and mixtures thereof. Linolenic acid or ricinoleic acid may be present.
- the cation forming the salt or soap with the fatty acid usually is sodium, potassium or ammonium. Practically, it is possible to use an unsaturated fatty acid having 18 carbon atoms in admixture with a small amount of a saturated fatty acid having about 18 carbon atoms.
- Particularly preferred is a mixture of the salts of oleic acid and linoleic acid.
- One of the most convenient mixture of the salt contains from about 50 to about 80% by weight of oleic acid and 40 to 5% by weight of linoleic acid, the balance being a small amount, say, at most 20% by weight of, a saturated fatty acid, for example, palmitic acid and stearic acid.
- the proportions of insecticide (a) to fatty acid (b) may range from about 1:200 to about 1:1 by wt., preferably about 1:20 to about 1:2.
- the mixture may be used in the form of a solution in any suitable solvent.
- an aqueous solution is used in which the concentration of insecticide (a) ranges from about 0.0005 to about 5% preferably from about 0.005 to about 0.1% by wt., and the concentration of fatty acid or its salt (b) ranges from about 0.05 to about 5, preferably from about 0.1 to about 1% by wt.
- the soap of PG,5 the fatty acid is used in aqueous solution.
- Suitable insecticidal esters of phosphoric and thiophosphoric acids include diazinon® [phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester], malation [S-(1,2-dicarbethoxyethyl)-O,O-dimethyldithiophosphate], phosphamedon.
- Suitable carbamate insecticides include carbaryl(servin®) [1-naphthyl-N-methylcarbamate)], pirimicarb 2(dimethylamino)-5,6-dimethyl-4-pyrimidyl dimethylcarbamate.
- the unsaturated fatty acid (b) used according to the present invention is biodegradable and the amount of the synthetic insecticide (a) may be substantially reduced in order to obtain satisfactory insecticidal results, it is expected that the present invention will, at least partly, the environmental problem which has arisen as a result of the massive use of the synthetic insecticide (a) which is hardly biodegradable.
- the standardized plate method (see example 1) was used in testing the solutions with ca. 3 ml of solution being applied per replicate. Mortality assessments were made 24 and 48 hours after treatments.
- Each treatment consisted of three replicates, with the treatment solutions applied to the tent and caterpillars, using a 750 ml hand-held trigger spray pump and sprayed until the setae of the larvae were wet (ca. 50-60 ml of solution/tent).
- the weather was clear and sunny, 19°-20° C. with a 3-4 km hr. breeze and with no rain occurring during the experiment.
- Insects were treated topically to wetting with a hand pump sprayer and returned to rearing containers. Mortality was assessed after 24 hours at room temperature.
- a standard retail grade of pirimicarb (Pirimor®) formulated as a 50% WP was used in the tests.
- Treatments were applied with a hand-pump sprayer (Green Cross Super Spray 6X-60®, with each plant sprayed to wetting (ca. 10 mls treatment solution). Each treatment consisted of four replicates with one plant per replicate. Aphid mortality was assessed twenty-four hours after treatment with twenty-five aphids counted per replicate.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Mixtures of organic insecticides of the organophosphate types or of the carbamate type, with certain fatty acids or their salts, have been found to have enhanced insecticidal activity. The fatty acids found operative are the unsaturated 18-carbon atom ones. The mixtures are toxic to both sucking insects and defoliators. The weight ratio of organophosphate or carbamate to fatty acid can range from about 1:1 to about 1:200 respectively. The amounts of the organophosphate or carbamate required for substantial effectiveness can be reduced significantly by concurrent use of the fatty acid. The fatty acid is more environmentally acceptable than the other types of insecticides mentioned. This unique composition can be used to protect against a broader range of insects.
Description
This is a continuation of application Ser. No. 722,460, filed Apr. 12, 1985, now abandoned.
This invention is concerned with insecticides and enhancing their insecticidal effect using partial replacement compounds which are more environmentally acceptable.
One of the main means of controlling insect infestation has been through the use of chemical insecticides. At the present time there are 15,000 registered pesticides within North America of which about 6,000 are sold in Canada. The pesticides generally fall into five major categories viz: chlorinated hydrocarbons e.g. DDT, lindane, methoxychlor, etc.; organophosphates e.g. malathion, dibrom, diazinon (trademark), phosphamidon, etc.; carbamate compounds e.g. baygon (trademark), sevin (trademark), zectran (trademark), etc.; inorganic compounds e.g. arsenic, sulphur, borax, etc.; and botanical compounds e.g. pyrethrum, strychnine, nicotine, etc. The chemical insecticides have been frequently used against major forest pests, e.g. DDT against spruce budworm, and have in many cases, been quite successful.
The chemical insecticides, with the exception of the botanical ones, have several disadvantages. Most of them are highly toxic to fish, wildlife, and humans and must be used with caution. They are usually not natural biological constituents and tend to persist for long lengths of time after their initial application. This is best exemplified by the chlorinated hydrocarbons which because of their persistence have passed through the animal food chain and caused egg shell thinning and egg breakage in many species of birds.
Besides their initial toxic effect, these compounds can have sub-acute effects on non-target fauna and flora thereby causing biochemical, behavioural and physiological changes as well as reproductive failure. Most of the chemical insecticides are quite expensive and with the current petroleum shortage, difficult to obtain. The breakdown products and secondary metabolites of most petrochemical pesticides and their impact on humans and other living organisms are poorly understood.
Recent research has shown that the unsaturated C18 fatty acids or their salts (C18:X) are highly toxic to soft bodied insects including aphids, mealybugs, whitefly, pear psylla, rose slugs, etc. (G. Puritch, 1978 Symposium on the Pharmacological Effects of Lipids AOCS monograph No. 5, 105-112). During investigations, it was further discovered that combination of the unsaturated 18 carbon fatty acids and/or salts with either organophosphates or carbamate insecticides have an unexpectedly high degree of insecticidal activity when topically applied. This unique finding has permitted a reduction of the potrochemical pesticide required for suitable pest control and has provided an increase in the spectrum of insect pests controlled. For example, we found the C18:X acids, especially oleic and linoleic and their salts in solution in concentrations from 0.25 to 5.0% in combination with the organophosphates, especially diazinon in a concentration range of 50 ppm to 50,000 ppm, were effective for the control of insect pests.
The invention thus provides an insecticidal composition having enhanced insecticidal activity comprising:
(a) an insecticide active against defoliating insects selected from the group consisting of organic esters of phosphoric or thiophosphoric acid and carbamates, and mixtures thereof, and
(b) an unsaturated fatty acid having 18 carbon atoms or its salt; the fatty acid being at least about 50% by weight of (a)+(b).
The invention includes a method of protecting susceptible plants against sucking insects or defoliating insects applying concurrently to the plant surfaces or directly to the insects, both (a) an insecticide active against defoliating insects selected from organic esters of phosphoric or thiophosphoric acids and carbamates, and mixtures thereof, and (b) an unsaturated fatty acid having 18 carbon atoms or its salt; the fatty acid compound being at least about 50% by wt. of (a)+(b). Preferably (a) and (b) are applied together as a mixture.
The invention also includes a method of synergistically enhancing the insecticidal activity of an insecticide selected from the group consisting of organic esters of phosphoric or thiophosphoric acid and carbamates and carbamates and mixtures thereof, the method comprises adding to the insecticide an effective amount of a unsaturated fatty acid having 18 carbon atoms. In any case, the amount of the unsaturated fatty acid is at least the same amount as the insecticide.
The fatty acid (b) is preferably selected from oleic acid, linoleic acid, their soaps (salts) and mixtures thereof. Linolenic acid or ricinoleic acid may be present. The cation forming the salt or soap with the fatty acid usually is sodium, potassium or ammonium. Practically, it is possible to use an unsaturated fatty acid having 18 carbon atoms in admixture with a small amount of a saturated fatty acid having about 18 carbon atoms.
Particularly preferred is a mixture of the salts of oleic acid and linoleic acid. One of the most convenient mixture of the salt contains from about 50 to about 80% by weight of oleic acid and 40 to 5% by weight of linoleic acid, the balance being a small amount, say, at most 20% by weight of, a saturated fatty acid, for example, palmitic acid and stearic acid.
In the composition, or in use, the proportions of insecticide (a) to fatty acid (b) may range from about 1:200 to about 1:1 by wt., preferably about 1:20 to about 1:2.
The mixture may be used in the form of a solution in any suitable solvent. In one preferred embodiment an aqueous solution is used in which the concentration of insecticide (a) ranges from about 0.0005 to about 5% preferably from about 0.005 to about 0.1% by wt., and the concentration of fatty acid or its salt (b) ranges from about 0.05 to about 5, preferably from about 0.1 to about 1% by wt. Preferably the soap of PG,5 the fatty acid is used in aqueous solution.
Other detergents, wetting agents, carriers, adjuvants, etc., may be used as known in the art.
Suitable insecticidal esters of phosphoric and thiophosphoric acids include diazinon® [phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester], malation [S-(1,2-dicarbethoxyethyl)-O,O-dimethyldithiophosphate], phosphamedon.
Suitable carbamate insecticides include carbaryl(servin®) [1-naphthyl-N-methylcarbamate)], pirimicarb 2(dimethylamino)-5,6-dimethyl-4-pyrimidyl dimethylcarbamate.
Because the unsaturated fatty acid (b) used according to the present invention is biodegradable and the amount of the synthetic insecticide (a) may be substantially reduced in order to obtain satisfactory insecticidal results, it is expected that the present invention will, at least partly, the environmental problem which has arisen as a result of the massive use of the synthetic insecticide (a) which is hardly biodegradable.
Test of unsaturated C18 salts (SIS=oleate/linoleate, 77%:7%) in combination with the organophosphate insecticide, diazinon® [phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester] for the control of the cabbage aphid, Brevicoryne brassicae (L.).
Twenty treatments, five replicates per treatment were applied to cabbage aphids, B. brassicae (L.) using the standardized plate method. This method entailed placing greater than twenty insects per replicate onto a glass plate (40×40 cm) and applying approximately 1 ml of treatment solution per replicate using a 10 cc plastic syringe equipped with a furnace-burner-tip nozzle (Monarch 0.75 GPH, 45° A.R.). One minute after the spray was applied, twenty insects were transferred to filter paper-lined petri plates. Petri plates were left covered with mortality assessments made 24 hours post-tretment discounting parasitized aphids and potato aphids, Macrosiphum euphorbiae (Thomas). Treatments applied were (% a.i.*):
______________________________________
(1) Tap water control (= diluent)
(11) 0.1% SIS + 0.0025
(2) 0.1. SIS (12) 0.1 SIS + 0.005 DZ
(3) 0.25 SIS (13) 0.25 SIS + 0.0005 DZ
(4) 0.5 SIS (14) 0.25 SIS + 0.001 DZ
(5) 0.0005 DZ (15) 0.25 SIS + 0.0025 DZ
(6) 0.001 DZ (16) 0.25 SIS + 0.005 DZ
(7) 0.0025 DZ (17) 0.50 SIS + 0.0005 DZ
(8) 0.005 DZ (18) 0.50 SIS + 0.001 DZ
(9) 0.1 SIS + 0.0005 DZ
(19) 0.50 SIS + 0.0025 DZ
(10) 0.1 SIS + 0.001 DZ (20) 0.50 SIS + 0.005 DZ
______________________________________
The results are listed in Table 1. All of the unsaturated C18 salts (SIS)-diazinon combinations gave higher mortality than the sum of the mortalities obtained for SIS or diazinon alone, thus they acted synergistically (Table 1).
TABLE 1
__________________________________________________________________________
Observed and corrected mortality of the cabbage aphid, Brevicoryne
brassicae (L.) to treatment solutions of
SIS and Diazinon at various concentrations of active ingredient.
Assessments made 24 hours post-treatment. -
Abbott's
Expected
Mortality Per Replicate
Percent Corrected
Additive
Treatment 1 2 3 4 5 Mortality
Mortality
Mortality
__________________________________________________________________________
0.1 SIS + 0.005 DZ
20/20
20/20
20/20
20/20
20/20
100
a.sup.1
100.sup.2
52.3
0.5 SIS + 0.005 DZ
20/20
20/20
20/20
20/20
20/20
100
a 100.sup.2
84.8
0.5 SIS + 0.0005 DZ
19/20
20/20
18/18
19/19
20/20
99.0
a 98.8.sup.2
70.7
0.25 SIS + 0.0025 DZ
20/20
19/19*
19/19*
18/19*
20/20
99.0
a 98.8.sup.2
56.9
0.5 SIS + 0.001 DZ
20/20
20/20
18/20
20/20
20/20
98.0
a 97.7.sup.2
68.2
0.25 SIS + 0.001 DZ
20/20
20/20
18/20
18/18*
19/19*
97.9
a 97.5.sup.2
33.5
0.1 SIS + 0.0025 DZ
18/18*
18/18*
18/19*
20/20
19/20*
97.9
a 97.5.sup.2
59.1
0.5 SIS + 0.0025 DZ
17/20
20/20
20/20
20/20
19/19*
97.0
a 96.5.sup.2
91.6
0.25 SIS + 0.005 DZ
17/20
19/20
20/20
20/20
20/20
96.0
a 95.3.sup.2
50.1
0.1 SIS + 0.0005 DZ
12/19
19/20
18/20
17/17*
18/19
88.4
ab
86.5.sup.2
38.2
0.25 SIS + 0.0005 DZ
13/19*
14/20
17/20
16/20
19/19*
80.6
b 77.4.sup.2
36.0
0.1 SIS + 0.001 DZ
19/19*
19/20
13/19*
10/19*
13/17*
78.7
b 75.1.sup.2
35.7
0.5 SIS 10/22
9/15*
9/20*
8/19*
14/20
58.1
c 43.8.sup.
0.0025 DZ 11/20
10/20
10/20
12/18*
9/16*
55.3
c 47.8.sup.
0.005 DZ 5/15*
8/19*
7/15*
7/16*
14/18*
49.4
cd
41.0.sup.
0.0005 DZ 5/20
8/19
6/20
9/20
9/20
37.4
de
26.9.sup.
0.001 DZ 8/16
6/15*
6/19*
4/20
7/18*
35.2
e 24.4.sup.
0.1 SIS 1/19*
3/19*
5/19
2/20
5/19*
24.0
f 11.3.sup.
0.25 SIS 6/20
3/15
4/18*
1/4*
3/20
22.1
f 9.1
Control-tap water
1/17
4/18*
1/20
2/18
4/11*
14.3
f 0
(= diluent)
__________________________________________________________________________
*Total # (20) of aphids altered due to discounting aphid parasitism and
presence of the potato aphid.
.sup.1 Means followed by the same letter are not significantly different
at the 5% alpha level as determined by Duncan's multiple range test.
.sup.2 Mortality values (corrected) followed by the superscript 2 are
greater than additive i.e. synergistic
Test of unsaturated C18 salts (SIS=oleate/linoleate, 77%:7%) in combination with the organophosphate insecticide, diazinon® [Phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester] for the control of the larval form of the tent caterpillar, Malacosoma californicum pluviale (Dyar) tested in vitro.
Tent caterpillars, Malacosoma californicum pluviale (Dyar) were field collected from their hawthorn host, Crataegus douglasii L. and brought to an entomology laboratory where they were caged and fed prior to testing. Five replicates per treatment with each replicate containing five caterpillars were randomly assigned to the following treatments (% a.i.):
______________________________________
1. water control (diluent)
11. 0.1 SIS + 0.001 DZ
2. control (untreated)
12. 0.1 SIS + 0.0025 DZ
3. 0.1 SIS 13. 0.1 SIS + 0.005 DZ
4. 0.25 SIS 14. 0.25 SIS + 0.0005 DZ
5. 0.5 SIS 15. 0.25 SIS + 0.001 DZ
6. 0.0005 DZ 16. 0.25 SIS + 0.0025 DZ
7. 0.001 DZ 17. 0.25 SIS + 005 DZ
8. 0.0025 DZ 18. 0.5 SIS + 0.0005 DZ
9. 0.005 DZ 19. 0.5 SIS + 0.001 DZ
10. 0.1 SIS + 0.0005 DZ
20. 0.5 SIS + 0.0025 DZ
21. 0.5 SIS + 0.005 DZ
______________________________________
The standardized plate method (see example 1) was used in testing the solutions with ca. 3 ml of solution being applied per replicate. Mortality assessments were made 24 and 48 hours after treatments.
TABLE 2
______________________________________
Mortality of tent caterpillar larvae, Malacosoma
californicum pluviale (Dyar) to treatment solutions of
SIS and Diazinon at various concentrations of active
ingredient. Assessment made 48 hrs. post-treatment.
Date Mort. Per Rep. (X/5)
%
of Trt.
Treatment 1 2 3 4 5 Mort.
______________________________________
June Control-tap water
0 0 0 0 0 0.0
5/84 Control-untreated
0 0 0 0 0 0.0
0.1 SIS 0 0 0 0 0 0.0
0.25 SIS 1 0 0 1 1 12.0
0.50 SIS 0 1 0 0 0 4.0
0.0005 DZ 0 0 0 0 0 0.0
0.001 DZ 0 0 0 0 0 0.0
0.0025 DZ 0 0 1 0 2 12.0
0.005 DZ 4 3 4 2 3 64.0
0.1 SIS + 0.0005 DZ
3 2 4 0 2 55.0
0.1 SIS + 0.001 DZ
2 2 2 1 3 40.0
0.1 SIS + 0.0025 DZ
5 4 5 5 5 96.0
0.1 SIS + 0.005 DZ
5 5 4 5 5 96.0
0.25 SIS + 0.0005 DZ
3 3 1 2 3 48.0
0.25 SIS + 0.001 DZ
3 3 2 3 5 64.0
0.25 SIS + 0.0025 DZ
4 3 1 4 4 64.0
0.25 SIS + 0.005 DZ
5 4 5 5 5 96.0
0.50 SIS + 0.0005 DZ
4 4 2 5 5 80.0
0.50 SIS + 0.001 DZ
3 4 5 5 2 76.0
0.50 SIS + 0.0025 DZ
5 5 4 4 5 92.0
0.50 SIS + 0.005 DZ
5 5 5 5 5 100.0
______________________________________
TABLE 3
______________________________________
Expected values (additive) versus observed values of
percent mortalities obtained for tent caterpillar
larvae, Malacosoma californicum pluviale (Dyar) when
treated with different SIS/DZ combinations. Expected
values were calculated from results of SIS and DZ alone.
Observed Expected Additive
Treatment Mortality
Mortality
______________________________________
0.1 SIS + 0.0005 DZ
55* 0
0.1 SIS + 0.001 DZ
40* 0
0.1 SIS + 0.0025 DZ
96* 12
0.1 SIS + 0.005 DZ
96* 64
0.25 SIS + 0.0005 DZ
48* 12
0.25 SIS + 0.001 DZ
64* 12
0.25 SIS + 0.0025 DZ
64* 24
0.25 SIS + 0.005 DZ
96* 76
0.50 SIS + 0.0005 DZ
80* 4
0.50 SIS + 0.001 DZ
76* 4
0.50 SIS + 0.0025 DZ
92* 16
0.50 SIS + 0.005 DZ
100* 68
______________________________________
*Numerical values followed by an asterisk are significantly greater than
the expected additive values.
All of the unsaturated C18 salts (SIS)-diazinon combinations gave higher mortalities than the sum of the mortalities obtained for SIS or diazinon alone in the control of the larval form of the tent caterpillar, thus they acted synergistically (Table 3).
Test of unsaturated C18 salts (SIS=oleate/linoleate, 77%:7%) in combination with the organophosphate insecticide, diazinon® [phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimdinyl)ester] for the control of tent caterpillars, Malacosoma californicum pluviale (Dyar) tested in situ.
Tent caterpillars, Malacosoma californicum pluviale (Dyar) in various larval instars in their tents were tagged in the field on their host plant hawthorn, and randomly assigned to the following treatments (% a.i.):
______________________________________
1. Water control (= diluent)
6. 0.1 DZ
2. 1.0 SIS 7. 1.0 SIS + 0.0025 DZ
3. 0.0025 DZ 8. 1.0 SIS + 0.005 DZ
4. 0.005 DZ 9. 1.0 SIS + 0.01 DZ
5. 0.01 DZ 10. 1.0 SIS + 0.1 DZ
______________________________________
Each treatment consisted of three replicates, with the treatment solutions applied to the tent and caterpillars, using a 750 ml hand-held trigger spray pump and sprayed until the setae of the larvae were wet (ca. 50-60 ml of solution/tent). The weather was clear and sunny, 19°-20° C. with a 3-4 km hr. breeze and with no rain occurring during the experiment.
Synergistic effects of unsaturated C18 salts (SIS) and diazinon combinations were observed after treating tent caterpillars, Malacosoma californicum pluviale (Dyar) on trees in field conditions (Table 4). The combinations of 1.0% SIS with (1) 0.0025 DZ; (2) 0.005 DZ or (3) 0.01 DZ gave higher mortality than the sum of the mortalities of the components (i.e. SIS+diazinon) alone, thus they acted synergistically.
TABLE 4
______________________________________
Mortality of tent caterpillar larvae, Malacosoma
californicum pluviale (Dyar) to treatment solutions of
SIS and Diazinon at various concentrations of active
ingredient tested in field conditions. Assessments
made 24 hours post-treatment.
Expected
Replicates % Additive
Treatment 1 2 3 Mort. Mortality
______________________________________
water control
2/38 1/74 0/8 2.50
(diluent)
1.0 SIS 1/31 6/49 2/15 9.47
0.0025 DZ 1/78 1/4 1/11 3.22
0.005 DZ 0/2 .sup.1 2/28 6.67
0.01 DZ 6/14 6/21 0/10 26.7
0.1 DZ 7/7 32/32 53/60 92.9
1.0 SIS + 10/13 22/25 9/35 56.2* 12.69
0.0025 DZ
1.0 SIS + 0.005 DZ
4/40 6/6 6/15 26.2* 16.14
1.0 SIS + 0.01 DZ
1/1 38/50 4/12 71.4* 36.17
1.0 SIS + 0.1 DZ
46/49 7/7 28/30 94.2 >100
______________________________________
.sup.1 Caterpillars had moved off leaving none in the tent so observation
counted as missing.
*Values with an asterisk had mortalities greater than additive
mortalities, thus acted synergistically.
Test of unsaturated C18 salts (SIS=oleate/linoleate, 77%:7%) in combination with the organophosphate insecticide, diazinon for the control of the greenhouse whitefly, Trialeurodes vaporariorum Westwood.
Adult whitefly were vacuum aspirated into 30 dram vials, with 20-40 whitefly per vial. One vial of whitefly at a time was cooled at 0° C. in a freezer for 2-3 minutes, contents tapped into cooled filter-paper-lined petri plates, and sprayed with ca. 2 mls of one of the following treatment solutions, using a plastic disposable syringe sprayer adapted to a furnace-burner-tip-nozzle (Monarch 0.75 GPH, 45°AR) (a.i.):
1. Tap water control (=diluent)
2. 0.25% SIS
3. 0.0025% DZ
4. 0.25% SIS+0.0025% DZ
After treatment, the exact whitefly number was recorded per petri plate, the cover placed on the dish and left 24 hours until assessment.
A higher mortality of whitefly adults (98.8%) was obtained in the combination of 0.25% SIS with 0.0025% DZ than the sum of the mortalities of the components alone (90.2%) indicating a synergistic interaction between the 0.25% SIS and 0.0025% DZ (Table 5).
TABLE 5
__________________________________________________________________________
Mortality of the adult form of the greenhouse whitefly, Trialeurodes
vaporariorum
Westwood caused by treatments of unsaturated C18 salt (SIS) and the
organophosphate,
diazinon applied alone or in combination. Mortality was assessed 24 hours
post treatment.
% Mort.
Replicate (% Mortality) Abbott's
Treatment 1 2 3 4 5 % Mort. ± S.E.
Correct.
__________________________________________________________________________
Tap water control
64.7
22.2
41.5
18.4
36.1
36.6 ± 18.4
0
(= diluent)
0.25% SIS 89.3
82.8
97.4
84.0
84.4
87.6 ± 6.1
81.4
0.0025% DZ 71.0
79.2
28.6
43.3
10.0
46.4 ± 28.9
8.8
0.25% SIS + 0.0025 DZ
100 100 96.2
100 100 99.2 ± 1.7
98.8*
__________________________________________________________________________
*Mortality value followed by an astezisk is greater than the additive
value of the two components alone, thus 0.25% SIS and 0.0025% DZ acted
synergistically.
Test of unsaturated C18 fatty acid salts (soaps) in combination with diazinon® for control of earwigs (Forficula auricularia).
Adults F. auricularia were collected from the field and separated into groups of 25. Three replicates of each group were assigned to the following treatments (a.i.):
(a) water
(b) 0.8% C18:1+C18:2 (77:7%) salts (SIS)
(c) 0.1 Diazinon® (DZ)
(d) 0.8% SIS+0.01% DZ
Insects were treated topically to wetting with a hand pump sprayer and returned to rearing containers. Mortality was assessed after 24 hours at room temperature.
Results are given in Table 6.
TABLE 6
______________________________________
% Mortality
Treatment Rep 1 Rep 2 Rep 3 Rep 4 Rep 5 Ave.
______________________________________
Control 0* 0 0 0 0 0
0.8% SIS 20 40 20 40 0 24
0.01% DZ 20 8 12 16 8 12.8
0.8% SIS +
100 92 100 100 100 98.4
0.01% DZ
______________________________________
*% Mortality out of 25 insects.
These results clearly show the synergism between the fatty acid salts and
diazinon ®.
Test of unsaturated C18 salts (BIS=oleate/linoleate, 54.0%:43.0%) in combination with the carbamate insecticide, pirimicarb for the control of the cabbage aphid, Brevicoryne brassicae (L.).
Cabbage, Lactuca sativa L.c.v. "Penn State Baldhead".
Twenty four cabbage plants, eight weeks in age, which were infested with the cabbage aphid, B. brassicae (L.) were selected from a commercial field (Mr. Ian Vantreight, 4423 Tyndall Road, Victoria, B.C.) and brought back to a greenhouse for testing. These plants were replanted and randomly assigned to the following treatments (% a.i.):
(a) Tap water control (=diluent for treatments)
(b) 0.06% BIS
(c) 0.13% BIS
(d) 0.006% pirimicarb (1/8 the label rate)
(e) 0.006% pirimicarb+0.06% BIS
(f) 0.006% pirimicarb+0.13% BIS
These solutions were made up fresh before use. The unsaturated fatty acid salts were made by neutralizing oleic and linoleic (BIS=54.0%:43.0%) with potassium hydroxide. A standard retail grade of pirimicarb (Pirimor®) formulated as a 50% WP was used in the tests. Treatments were applied with a hand-pump sprayer (Green Cross Super Spray 6X-60®, with each plant sprayed to wetting (ca. 10 mls treatment solution). Each treatment consisted of four replicates with one plant per replicate. Aphid mortality was assessed twenty-four hours after treatment with twenty-five aphids counted per replicate.
A significant treatment effect (P<0.01%) was obtained from analysis of variance of the data, with the pirimicarb BIS combinations providing greater control of the cabbage aphid than each of the components (i.e. BIS and pirimicarb) alone (Table 7). By comparing the expected additive mortalities of the pirimicarb and BIS treatments (4% and 5%) with the observed mortalities (80% and 85%) of the two pirimicarbs/BIS combinations, the synergistic interaction of the BIS with the pirimicarb is clearly evident. The pirimicarb/BIS combinations gave higher motality than the sum of the mortalities obtained for pirimicarb and BIS alone, thus they act synergistically.
TABLE 7
__________________________________________________________________________
Effect of the carbamate insecticide, pirimicarb and the C18 fatty acid
salt (BIS) on cabbage aphid mortality.
Aphid Mortality (X/25) per
Standard Expected
replicate Mean # Dead
Error
% Mortality
Additive
Treatment 1 2 3 4 (X/25) (±)
Obtained
Mortality
__________________________________________________________________________
Tap water control (= diluent)
0 0 2 0 0.5 1.0 2 a*
0.06% a.i. BIS 0 2 1 0 0.75 0.96 3 a
0.13% a.i. BIS 2 1 1 0 1.0 0.82 4 a
0.006% a.i. pirimicarb
1 0 0 0 0.25 0.5 1 a
0.006% a.i. pirimicarb +
19 20 21 20 20 0.82 80 b 4
0.06% BIS
0.006% pirimicarb +
21 20 21 23 21.25 1.26 85 b 5
0.13% BIS
__________________________________________________________________________
FS = 473.5**; Fc(5, 18)0.01 = 5.07
*Means followed by the same letter are not significantly different at the
5% alpha level using Duncans Multiple Range Test.
**Significant to the 0.01 alpha level
Claims (23)
1. An insecticidal composition having synergistic insecticidal activity, consisting essentially of:
(a) an insecticide active against defoliating insects, said insecticide being selected from the group consisting of phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester, 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl dimethylcarbamate, and 1-naphthyl N-methylcarbamate; and
(b) an unsaturated fatty acid having 18 carbon atoms or its salt, which is selected from the group consisting of oleic acid, linoleic acid, their salts and mixtures thereof,
wherein the weight proportion of said insecticide (a): said unsaturated fatty acid or its salt (b) is from about 1:1,000 to about 1:1.
2. The composition of claim 1, wherein component (b) is sodium, potassium or ammonium salt of a fatty acid selected from the group consisting of oleic acid, linoleic acid and a mixture thereof.
3. The composition of claim 1, wherein component (b) is sodium, potassium or ammonium salt of a fatty acid mixture of oleic acid and linoleic acid.
4. The composition of claim 1, wherein component (b) is potassium salt of a fatty acid selected from the group consisting of oleic acid, linoleic acid, and a mixture thereof.
5. The composition of claim 2, wherein the weight proportion of said insecticide (a): said unsaturated fatty acid salt (b) is from about 1:1,000 to about 1:2.
6. The composition of claim 2, wherein the weight proportion of said insecticide (a): said unsaturated fatty acid salt (b) is from about 1:1,000 to about 1:20.
7. The composition of claim 2, wherein the weight proportion of said insecticide (a): said unsaturated fatty acid or its salt (b) is from about 1:200 to about 1:2.
8. The composition of claim 2 in the form of an aqueous solution in which the concentration of the insecticide (a) ranges from about 0.005 to about 5% by wt. and the concentration of the fatty acid or its salt (b) ranges from about 0.05 to about 5% by wt.
9. The composition of claim 1 wherein the insecticide (a) comprises 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl dimethylcarbamate.
10. The composition of claim 5 wherein the insecticide (a) comprises 2-(dimethylamino)-5,6 dimethyl-4-pyrimidinyl dimethylcarbamate.
11. The composition of claim 1 wherein the insecticide (a) comprises phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester.
12. The composition of claim 5 wherein the insecticide (a) comprises phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester.
13. The composition of claim 1 wherein the insecticide (a) comprises 1-naphthyl N-methylcarbamate.
14. The composition of claim 5 wherein the insecticide (a) comprises 1-naphthyl N-methylcarbamate.
15. A method of protecting susceptible plants against defoliating insects, which method comprises applying to the plant surfaces or directly to the insects, an insecticidally effective amount of a composition having synergistic insecticidal properties consisting essentially of both (a) an insecticide active against defoliating insects, said insecticide being selected from the group consisting of phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester, 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl dimethylcarbamate, and 1-naphthyl N-methylcarbamate; and (b) an unsaturated fatty acid having 18 carbon atoms or its salt, which is selected from the group consisting of oleic acid, linoleic acid, their salts and mixtures thereof,
wherein the weight proportion of said insecticide (a): said unsaturated fatty acid or its salt (b) is from about 1:1,000 to about 1:1, whereby said composition has an insecticidal effect greater than the additive effect of ingredients (a) and (b).
16. The method of claim 15, wherein component (b) is sodium, potassium or ammonium salt of a fatty acid selected from the group consisting of oleic acid, linoleic acid and a mixture thereof.
17. The method of claim 16, wherein the weight proportion of said insecticide (a): said unsaturated fatty acid salt (b) is from about 1:1,000 to about 1:2.
18. The method of claim 16, wherein the mixture is in an aqueous solution containing from about 0.005 to about 5% by weight of the insecticide (a) and from about 0.05 to about 5% by weight of the fatty acid or sodium, potassium or ammonium salt thereof, provided that the proportion of (a):(b) by weight ranges from 1:1,000 to 1:20.
19. The method of claim 18, wherein the fatty acid (b) is a mixture consisting essentially of 50% to 80% by weight of oleic acid and 40% to 5% by weight of linoleic acid or sodium, potassium or ammonium salt of the acid mixture.
20. The method of claim 17 wherein the insect is selected from the group consisting of cabbage aphid, tent caterpillar, white fly, and earwig.
21. The method of claim 17 wherein the insecticide (a) comprises 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl dimethylcarbamate.
22. The method of claim 17 wherein the insecticide (a) comprises phosphorothioic acid O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)ester.
23. The method of claim 17 wherein the insecticide (a) comprises 1-naphthyl N-methylcarbamate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/118,305 US4774234A (en) | 1985-04-12 | 1987-11-06 | Insecticide mixtures containing fatty acids |
| US07/218,093 US4861762A (en) | 1985-04-12 | 1988-07-12 | Insecticide mixtures containing fatty acids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72246085A | 1985-04-12 | 1985-04-12 | |
| US07/118,305 US4774234A (en) | 1985-04-12 | 1987-11-06 | Insecticide mixtures containing fatty acids |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US72246085A Continuation | 1985-04-12 | 1985-04-12 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/218,093 Continuation US4861762A (en) | 1985-04-12 | 1988-07-12 | Insecticide mixtures containing fatty acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4774234A true US4774234A (en) | 1988-09-27 |
Family
ID=26816203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/118,305 Expired - Lifetime US4774234A (en) | 1985-04-12 | 1987-11-06 | Insecticide mixtures containing fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4774234A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4904645A (en) * | 1988-01-27 | 1990-02-27 | Safer, Ltd. | Environmentally safe, broad spectrum insecticide |
| US4983591A (en) * | 1988-01-27 | 1991-01-08 | Safer, Ltd. | Environmentally safe, broad spectrum insecticide |
| US5047424A (en) * | 1988-10-03 | 1991-09-10 | Safer, Inc. | Environmentally safe insecticide |
| US5614203A (en) * | 1995-01-30 | 1997-03-25 | Environmentally Safe Systems, Inc. | Environmentally safe pesticide and plant growth accelerator |
| US5631290A (en) * | 1993-02-18 | 1997-05-20 | W. Neudorff Gmbh | Fatty acid salt pesticidal composition |
| US5919733A (en) * | 1997-04-04 | 1999-07-06 | W. Neudorff Gmbh Kg | Non-staining herbicidal soap |
| US6103768A (en) * | 1991-05-01 | 2000-08-15 | Mycogen Corporation | Fatty acid based compositions and methods for the control of plant infections and pests |
| ES2193872A1 (en) * | 2002-02-26 | 2003-11-01 | Benedicto Macario Quibus | Fruit tree insect, cheese mite and fungus combat composition consists of a fungicide, insecticide, liquid soap and water mixture in specific proportions |
| KR100432815B1 (en) * | 1995-08-18 | 2005-02-23 | 다우 아그로사이언시즈 엘엘씨 | Composition with bactericidal synergistic effect and bacterial growth control method using the same |
| US20070148203A1 (en) * | 2005-09-16 | 2007-06-28 | W. Neudorff Gmbh Kg | Insecticide and molluscicide composition and methods |
| US20070148204A1 (en) * | 2005-09-16 | 2007-06-28 | W. Neudorff Gmbh Kg | Wide spectrum insecticide and miticide composition |
| US20100310620A1 (en) * | 2008-02-20 | 2010-12-09 | James Gordon Campbell Hamilton | Insect attractants and their use in methods of insect control |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US708649A (en) * | 1899-09-08 | 1902-09-09 | John C Kessler | Insect-repellent. |
| US1589866A (en) * | 1924-11-17 | 1926-06-22 | Siegler Edouard Horace | Insecticide and process of preparing the same |
| US2345891A (en) * | 1941-09-30 | 1944-04-04 | Claude R Wickard | Synergists to aerosol insecticides |
| US3429970A (en) * | 1961-02-02 | 1969-02-25 | Hoffmann La Roche | Method of hindering the metamorphosis and reproduction of arthropodes |
| CA950357A (en) * | 1970-08-12 | 1974-07-02 | Mobil Oil Corporation | Deodorization of organothiophosphorus compounds |
-
1987
- 1987-11-06 US US07/118,305 patent/US4774234A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US708649A (en) * | 1899-09-08 | 1902-09-09 | John C Kessler | Insect-repellent. |
| US1589866A (en) * | 1924-11-17 | 1926-06-22 | Siegler Edouard Horace | Insecticide and process of preparing the same |
| US2345891A (en) * | 1941-09-30 | 1944-04-04 | Claude R Wickard | Synergists to aerosol insecticides |
| US3429970A (en) * | 1961-02-02 | 1969-02-25 | Hoffmann La Roche | Method of hindering the metamorphosis and reproduction of arthropodes |
| CA950357A (en) * | 1970-08-12 | 1974-07-02 | Mobil Oil Corporation | Deodorization of organothiophosphorus compounds |
Non-Patent Citations (5)
| Title |
|---|
| Puritch, Symposium on Pharmacological Effects of Lipids: AOCS Monograph, No. 5; pp. 105 112, (1978). * |
| Puritch, Symposium on Pharmacological Effects of Lipids: AOCS Monograph, No. 5; pp. 105-112, (1978). |
| Ruritch, Proceedings of the 23rd Annual Lower Mainland Horticultural Improvement Association Grower s Short Course, Feb. 11, 12 and 13, 1981, Abbottsford, British Columbia, Canada, pp. 53 67. * |
| Ruritch, Proceedings of the 23rd Annual Lower Mainland Horticultural Improvement Association Grower's Short Course, Feb. 11, 12 and 13, 1981, Abbottsford, British Columbia, Canada, pp. 53-67. |
| The Merck Index, 10th Ed., (1983), 1766, 2968, 5522, 7223 & 7371. * |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983591A (en) * | 1988-01-27 | 1991-01-08 | Safer, Ltd. | Environmentally safe, broad spectrum insecticide |
| US4904645A (en) * | 1988-01-27 | 1990-02-27 | Safer, Ltd. | Environmentally safe, broad spectrum insecticide |
| US5047424A (en) * | 1988-10-03 | 1991-09-10 | Safer, Inc. | Environmentally safe insecticide |
| US6103768A (en) * | 1991-05-01 | 2000-08-15 | Mycogen Corporation | Fatty acid based compositions and methods for the control of plant infections and pests |
| US5631290A (en) * | 1993-02-18 | 1997-05-20 | W. Neudorff Gmbh | Fatty acid salt pesticidal composition |
| US5614203A (en) * | 1995-01-30 | 1997-03-25 | Environmentally Safe Systems, Inc. | Environmentally safe pesticide and plant growth accelerator |
| KR100432815B1 (en) * | 1995-08-18 | 2005-02-23 | 다우 아그로사이언시즈 엘엘씨 | Composition with bactericidal synergistic effect and bacterial growth control method using the same |
| US5919733A (en) * | 1997-04-04 | 1999-07-06 | W. Neudorff Gmbh Kg | Non-staining herbicidal soap |
| US6258752B1 (en) | 1997-04-04 | 2001-07-10 | W. Neudorff Gmbh Kg | Non-staining herbicidal soap |
| ES2193872A1 (en) * | 2002-02-26 | 2003-11-01 | Benedicto Macario Quibus | Fruit tree insect, cheese mite and fungus combat composition consists of a fungicide, insecticide, liquid soap and water mixture in specific proportions |
| US20070148203A1 (en) * | 2005-09-16 | 2007-06-28 | W. Neudorff Gmbh Kg | Insecticide and molluscicide composition and methods |
| US20070148204A1 (en) * | 2005-09-16 | 2007-06-28 | W. Neudorff Gmbh Kg | Wide spectrum insecticide and miticide composition |
| US7964205B2 (en) | 2005-09-16 | 2011-06-21 | W. Neudorff Gmbh Kg | Insecticide and molluscicide composition and methods |
| US8007820B2 (en) | 2005-09-16 | 2011-08-30 | W. Neudorff Gmbh Kg | Wide spectrum insecticide and miticide composition |
| US20100310620A1 (en) * | 2008-02-20 | 2010-12-09 | James Gordon Campbell Hamilton | Insect attractants and their use in methods of insect control |
| US8277825B2 (en) | 2008-02-20 | 2012-10-02 | Keele University | Insect attractants and their use in methods of insect control |
| US8586068B2 (en) * | 2008-02-20 | 2013-11-19 | Keele University | Insect attractants and their use in methods of insect control |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69528581T2 (en) | NEW TRAP DEVICE FOR FRUIT FLIES | |
| DE69413440T2 (en) | Pesticide compositions based on salts of fatty acids | |
| Read | Enhanced microbial degradation of carbofuran and fensulfothion after repeated applications to acid mineral soil | |
| US4774234A (en) | Insecticide mixtures containing fatty acids | |
| EP2846636B1 (en) | Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs | |
| Lindquist et al. | Laboratory studies on sterilization of the boll weevil with apholate | |
| US4861762A (en) | Insecticide mixtures containing fatty acids | |
| Coppage et al. | Brain-acetylcholinesterase inhibition in a marine teleost during lethal and sublethal exposures to 1, 2-dibromo-2, 2-dichloroethyl dimethyl phosphate (Naled) in seawater | |
| Livingston et al. | Review of current literature concerning the acute and chronic effects of pesticides on aquatic organisms | |
| EP0265825B1 (en) | Use of disinfectants for combating and destroying parasitic latent forms | |
| CA1054934A (en) | Terpene phenol resin compositions containing organophosphorus pesticides | |
| AT391242B (en) | NEW PREPARATIONS AND METHOD FOR CONTROLLING SCRAPS | |
| Lemon | Laboratory evaluation of some organophosphorus insecticides against Tribolium confusum Duv. and T. castaneum (Hbst.)(Coleoptera, Tenebrionidae) | |
| DE69702905T2 (en) | POLYAMINIC ACID TO IMPROVE THE INSECTICIDE ABSORPTION | |
| DE3783935T2 (en) | PESTICIDAL COMPOSITIONS AND METHODS. | |
| CA1187409A (en) | Insecticide mixtures containing fatty acids | |
| Mauck et al. | Effects of water quality on deactivation and toxicity of Mexacarbate (Zectran®) to fish | |
| Gaines et al. | Toxicity of various sulphur and phosphorus compounds applied as sprays on spider mites and aphids | |
| US3105000A (en) | Organo-tin and organo-sulphur parasiticides | |
| Matsumura et al. | Classification of insecticides | |
| Johansen | Laboratory toxicity of several insecticides to the honey bee | |
| Lyon et al. | Laboratory tests of 55 insecticides on Douglas-fir tussock moth larvae | |
| EP1085805A1 (en) | Use of at least one acid from the citric acid cycle combined with glycerine as a pesticide | |
| Odera | Insecticidal Control of Pineus SP.(Homoptera: Adelgidae) in East Africa | |
| Scholler et al. | Integration of chemical control of cockroaches and biological control of stored-product moths |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| AS | Assignment |
Owner name: NEWORLD BANK FOR SAVINGS, MASSACHUSETTS Free format text: SECURITY INTEREST;ASSIGNOR:SAFER, INC.;REEL/FRAME:005221/0861 Effective date: 19891115 |
|
| AS | Assignment |
Owner name: STATE STREET BANK AND TRUST COMPANY, MASSACHUSETTS Free format text: SECURITY INTEREST;ASSIGNOR:SAFER, INC.;REEL/FRAME:005293/0021 Effective date: 19900228 Owner name: SAFER, INC., A DE CORP. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:NEWORLD BANK;REEL/FRAME:005293/0001 Effective date: 19900228 |
|
| AS | Assignment |
Owner name: SAFER LTD. Free format text: CHANGE OF NAME;ASSIGNOR:SAFER AGRO-CHEM LTD.;REEL/FRAME:005554/0069 Effective date: 19860618 Owner name: SAFER, INC. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST. CONFIRMATORY ASSIGNMENT EFFECTIVE 12/19/86;ASSIGNOR:SAFER, LTD.(FOR 152148 CANADA, INC.;REEL/FRAME:005554/0066 Effective date: 19901108 Owner name: SAFER LTD. Free format text: CHANGE OF NAME;ASSIGNOR:152148 CANADA INC.;REEL/FRAME:005554/0062 Effective date: 19871202 |
|
| AS | Assignment |
Owner name: SAFER, INC., A DE CORP. Free format text: MERGER;ASSIGNOR:SAFER MERGER, INC., A CORP. OF DE;REEL/FRAME:005576/0354 Effective date: 19870120 Owner name: SAFER MERGER, INC., A CORP. OF DE Free format text: CHANGE OF NAME;ASSIGNOR:SAFER LTD., A CORP. OF CANADA;REEL/FRAME:005576/0348 Effective date: 19870116 |
|
| FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| AS | Assignment |
Owner name: FBS BUSINESS FINANCE CORPORATION, MINNESOTA Free format text: SECURITY INTEREST;ASSIGNOR:SAFER, INC.;REEL/FRAME:006399/0168 Effective date: 19921026 |
|
| FEPP | Fee payment procedure |
Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| FEPP | Fee payment procedure |
Free format text: PAT HLDR NO LONGER CLAIMS SMALL ENT STAT AS SMALL BUSINESS (ORIGINAL EVENT CODE: LSM2); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| FPAY | Fee payment |
Year of fee payment: 8 |
|
| AS | Assignment |
Owner name: SAFER, INC., MINNESOTA Free format text: NOTICE OF RELEASE OF SECURITY INTEREST IN U.S. PATENTS;ASSIGNOR:FBS BUSINESS FINANCE CORPORATION;REEL/FRAME:008650/0825 Effective date: 19970501 |
|
| AS | Assignment |
Owner name: GENERAL ELECTRIC CAPITAL CORPORATION, ILLINOIS Free format text: PATENT SECURITY AGREEMENT;ASSIGNOR:SAFER, INC.;REEL/FRAME:008545/0923 Effective date: 19970502 |
|
| AS | Assignment |
Owner name: GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT, CO Free format text: SECURITY INTEREST;ASSIGNOR:SAFER, INC.;REEL/FRAME:010164/0311 Effective date: 19990714 |
|
| FPAY | Fee payment |
Year of fee payment: 12 |
|
| AS | Assignment |
Owner name: ANTARES CAPITAL CORPORATION, AS AGENT, ILLINOIS Free format text: SECURITY INTEREST;ASSIGNOR:NEW SAFER, INC.;REEL/FRAME:011277/0464 Effective date: 20001117 |
|
| AS | Assignment |
Owner name: NEW SAFER, INC., DELAWARE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT;REEL/FRAME:011356/0001 Effective date: 20001117 Owner name: NEW SAFER, INC., DELAWARE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GENERAL ELECTRIC CAPITAL CORPORATION;REEL/FRAME:011356/0012 Effective date: 20001117 Owner name: NEW SAFER, INC., DELAWARE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SAFER, INC.;REEL/FRAME:011356/0411 Effective date: 20001117 |
|
| AS | Assignment |
Owner name: SAFER, INC., PENNSYLVANIA Free format text: CHANGE OF NAME;ASSIGNOR:NEW SAFER, INC.;REEL/FRAME:011425/0552 Effective date: 20001212 |
|
| AS | Assignment |
Owner name: SAFER-ARGO CHEM, LTD., CANADA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PURITCH, GEORGE S.;CONDRASHOFF, SERGI F.;REEL/FRAME:014357/0689 Effective date: 19850412 |
|
| AS | Assignment |
Owner name: SAFER, INC., PENNSYLVANIA Free format text: RELEASE AND REASSIGNMENT;ASSIGNOR:ANTARES CAPITAL CORPORATION, AS AGENT;REEL/FRAME:014154/0753 Effective date: 20030610 |
|
| AS | Assignment |
Owner name: ANTARES CAPITAL CORPORATION, AS AGENT, ILLINOIS Free format text: SECURITY AGREEMENT;ASSIGNOR:SAFER, INC.;REEL/FRAME:014178/0636 Effective date: 20030610 |
|
| AS | Assignment |
Owner name: SAFER, INC., MASSACHUSETTS Free format text: RELEASE OF SECURITY INTEREST;ASSIGNOR:STATE STREET BANK AND TRUST COMPANY;REEL/FRAME:014102/0833 Effective date: 20031028 |
|
| AS | Assignment |
Owner name: ALLIED CAPITAL CORPORATION, DISTRICT OF COLUMBIA Free format text: SECURITY AGREEMENT;ASSIGNOR:SAFER, INC.;REEL/FRAME:016480/0611 Effective date: 20050211 |
|
| AS | Assignment |
Owner name: SAFER, INC., PENNSYLVANIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:ALLIED CAPITAL CORPORATION;REEL/FRAME:019767/0089 Effective date: 20070822 |
|
| AS | Assignment |
Owner name: ANTARES CAPITAL CORPORATION, AS AGENT, ILLINOIS Free format text: SECURITY AGREEMENT;ASSIGNOR:SAFER, INC.;REEL/FRAME:019767/0723 Effective date: 20070822 |